Lithium diisopropylamide → HCID 86655977, compound

HRID 333102Notes

Reaction equation

HRID 333102 reaction equation
C(O[C:4](=[O:29])[CH2:5][N:6]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH2:7][CH2:8][CH:9]=[N:10][C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])C.[Li+].CC([N-]C(C)C)C>C1COCC1.[Cl-].[NH4+]>[CH2:22]([O:21][C:19]([N:6]1[CH2:7][CH2:8][C@@H:9]2[C@H:5]1[C:4](=[O:29])[N:10]2[C@@H:11]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 67319893HCID 67319893, compound

Product 1

HCID 86655977HCID 86655977, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

2-{Benzyloxycarbonyl-[3-(1(R)-phenyl-ethylimino)-propyl]-amino}-acetic acid ethyl ester (0.909 g; 2.29 mmol) is dissolved in dry THF (20 ml). The reaction mixture is cooled to −78° C. and LDA (1.6 ml of a 2M solution in THF) is added slowly. The reaction mixture is stirred for 6 hours at −78° C. Then, the reaction mixture is poured in chilled saturated aqueous ammonium chloride solution and extracted with ethyl acetate; the phases are separated. The aqueous phase is extracted twice with ethyl acetate (2 times 100 ml). The combined organic phases are washed with water (50 ml) and with brine twice (2 times 50 ml). The organic phase is dried over magnesium sulfate. The solids are filtered off and the solvent is removed under reduced pressure. The crude product is purified by column chromatography over silicagel (eluent: hexane/ethyl acetate 50:1 to 10:1). 0.418 g of a colorless yellow oil (yield 52%) are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe phases are separated
  3. extractionThe aqueous phase is extracted twice with ethyl acetate (2 times 100 ml)
  4. washThe combined organic phases are washed with water (50 ml) and with brine twice (2 times 50 ml)
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationThe solids are filtered off
  7. customthe solvent is removed under reduced pressure
  8. customThe crude product is purified by column chromatography over silicagel (eluent: hexane/ethyl acetate 50:1 to 10:1)

Sources & evidence

ORD record
ord-15477eca8efc4d7d9ed5b9b9fefc5aeb
Source dataset
uspto-grants-2014_11
Patent number
US08877961B2

Reaction notes

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